5-tert-Butyl-2-(chloromethyl)-1,3-oxazole → N-[5-[[(5-tert-Butyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamide

HRID 1060250Notes

Reaction equation

HRID 1060250 reaction equation
[C:1]([S:4][C:5]1[S:9][C:8]([NH:10][C:11](=[O:13])[CH3:12])=[N:7][CH:6]=1)(=O)[CH3:2].CC(C)([O-])C.[K+].ClCC1[O:23][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:25][N:26]=1>C1COCC1>[C:27]([C:24]1[O:23][C:2]([CH2:1][S:4][C:5]2[S:9][C:8]([NH:10][C:11](=[O:13])[CH3:12])=[N:7][CH:6]=2)=[N:26][CH:25]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 129689745-tert-Butyl-2-(chloromethyl)-1,3-oxazoleHCID 22481077S-(2-(Acetylamino)-5-thiazolyl) ethanethioateHCID 23665647Potassium tert-butoxide

Product 1

HCID 5329665N-[5-[[(5-tert-Butyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamideYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 50 mg (0.23 mmol, Applied Chemical Laboratory) of N-[5-(acetylthio)-2-thiazolyl]acetamide in 10 mL of THF was added 0.25 mL of potassium tert-butoxide solution (1 M solution, 0.25 mmol) at rt under argon. The resulting suspension was stirred for 15 min at rt, then a solution of 59 mg of 2-(chloromethyl)-5-t-butyloxazole (0.34 mmol) in 1 mL of THF was added. The resulting mixture was stirred at rt for 16 h, concentrated under reduced pressure and purified by flash column chromatography (silica gel, 25×200 mm, 1:1 EtOAc/hexanes followed by 100% EtOAc) to give 44 mg (0.14 mmol, 61%) of N-[5-[[(5-t-butyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamide as a white solid.

Workup

  1. stirringThe resulting mixture was stirred at rt for 16 h
  2. concentrationconcentrated under reduced pressure
  3. custompurified by flash column chromatography (silica gel, 25×200 mm, 1:1 EtOAc/hexanes followed by 100% EtOAc)

Sources & evidence

ORD record
ord-efd2a8d6019848dda5b91fe3ce892e70
Source dataset
uspto-grants-2003_02
Patent number
US06521759B2

Reaction notes

Loading…